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United States Patent Office Patented July 22, 1958 1 2,844,551 United States Patent Office Patented July 22, 1958 1. 2 Another aluminum alcoholate which can be used is 2,844,551 the so-called c-aluminum ethylate. It is readily soluble ALUMNUM COMPOUNDS AND THE PROCESS in organic solvents and can be obtained, as described by OF PREPARENGTHEM Adkins (Journal of the American Chemical Society, Vol. Ludwig Orthner and Martin Reuter, Frankfurt am Main, 44, page 2178), from amalgamated aluminum by means Germany, assignors to Farbwerke Hoechst A. G...yor of absolutely anhydrous ethanol, or as described by mas Meister Lucius & Brining, Frankfurt am Main Child and Adkins (Journal of the American Chemical Hochst, Germany, a company of Germany Society, vol. 45, page 3014), by heating sparingly soluble 6-aluminum ethylate for 15 hours to 275 C. No Drawing. Application April 7, 1953 Further aluminum alcoholates which are suitable are Seria No. 347,399 those containing per 1 equivalent of aluminum less than 1 equivalent of organic radicals which are bound in an Clains priority, application Germany April 9, 1952 ethereal manner through oxygen. 14 Claims. (C. 260-18) As such radicals there can be used aliphatic, alicyclic, 5 aromatic, araliphatic and heterocyclic hydrocarbon radi The present invention relates to aluminum compounds cals, which may, if required, be substituted by non-acid and the process of preparing them. groups such as the keto or ester group, halogen atoms From German Patent No. 569,946 it is known to such as chlorine atoms, or the amino group, or the react aluminum alcoholates with carboxylic acids in carbon chain of which may be interrupted by hetero various proportions and subsequently to hydrolyze the 20 atoms such as oxygen, sulfur or nitrogen. There may reaction products with water. Thereby, well defined pri be mentioned, for example: methyl, ethyl, chloroethyl, mary, secondary, and tertiary aluminum carboxylates are dimethyl, aminoethyl, isopropyl, butyl, octyl, octadecyl, obtained. As far as the preparation of the primary and cyclohexyl, phenyl, naphthyl, benzyl, phenylethyl, fur secondary salts of the formulae furmethyl, and the like. Several of the radicals indi 25 cated above can be bound simultaneously to the alu oH OH minum. Especially suitable aluminum alcoholates are Al-OH Aro CO-R those containing per 1 equivalent of aluminum about 0.5 O CO-R O CO-R to 0.9 equivalent of those radicals which are bound in is concerned, the corresponding mono- and di-carboxylic an ethereal way. acid aluminum alcoholates of the formulae 30 The remaining valences of the aluminum, i. e. those which are not bound in an ethereal way, by means of o R o R oxygen, to organic radicals can be saturated for example with oxygen under linkage to further aluminum atoms, AkoO CO-RR Aloco-ROCO-R 35 or with halogen, hydroxyl or organic acid radicals such are probably formed at first. By the subsequent treat as acetyl, and in this case several similar or different ment with water, the alkoxy groups are replaced by hy radicals mentioned above can simultaneously satisfy the droxy groups. remaining valences of the aluminum. Now, we have found that valuable aluminum com As aluminum alcoholates which contain per 1 equiva pounds are obtained by reacting 1 mol of aluminum al lent of aluminum less than 1 equivalent of radicals which coholate with less than 1 mol of a monobasic organic 40 are bound in an ethereal way, by means of oxygen, there substance of acid nature which forms aluminum salts, may be employed, for instance, those the solubility of or with mixtures of such substances, if desired in the which in organic solvents has been improved by thermal presence of an indifferent solvent. or hydrolytic treatment of normal aluminum alcoholates If the reaction is carried out at low temperatures it is with splitting off of a part of the alkoxy groups, in most immaterial whether the aluminum alcoholate is first in 45 cases probably with linkage of aluminum atoms by way troduced and the mono-basic organic substances of acid of oxygen atoms. nature are then added or whether the aluminum al Among these aluminum alcoholates there may be men coholate is introduced into the mono-basic organic Sub tioned, for example, the aluminum ethylates obtained by stances of acid nature or the solutions thereof. thermal treatment and corresponding to the empirical The process may also be carried out in such a way 50 molecular formulae Al(OCH5)4O and Al(OCH3)6Oa, that the reaction is performed at a low temperature, for as described by Henle (Berichte der deutschen chemischen instance a temperature below 40 C., preferably at room Gesellschaft, vol. 53, page 720); the aluminum ethylate temperature, if desired while using only part of the com obtained by hydrolytic treatment, as described in Ger ponents, and the reaction product is then heated to man Patents Nos. 277,187 and 277,188, and containing higher temperatures, if desired while adding the rest of 55 about 2 ethoxyl radicals per atom of aluminum; the basic the components. By its stepwise condensation, this proc aluminum ethylate of the empirical molecular formula ess offers the advantage of a better control of the re Al(OH) (C2H5O)2 obtained by boiling with anhydrous action and thus allows a more uniform production on an alcohol with access of air, as described by Meerwein and industrial scale. Bersin ("Annalen,” vol. 476, page 132); the aluminum-di It is also possible to perform the entire reaction at 60 hydroxocyclohexanolate obtained, as described by Meer higher temperatures. In this case it may be advan Wein and Bersin ("Annalen," vol. 476, page 132) by heat tageous to apply an elevated pressure. ing aluminum-cyclohexanolate at 275 C.; the basic alumi In practicing the present invention, suitable aluminum num ethylate obtained, as described by Bersin (Disserta alcoholates include, for example, those derived from tion Konigsberg 1928), by boiling with not absolutely an low or medium aliphatic alcohols. There are mentioned, 65 hydrous ethanol, and containing about 2 ethoxyl groups for instance: aluminum methylate, aluminum ethylate, per atom of aluminum. There may be further mentioned aluminum propylate, aluminum isopropylate, aluminum those aluminum alcoholates which can be obtained from butylate, aluminum isobutylate, aluminum amylate, alu aluminum alcoholates by reaction with slightly hydrous minum hexylate, aluminum octylate, aluminum-2-ethyl alcohols according to the process described by Tischts 70 chenko (Chem. Zentralblatt 1900, I, page 12). butylate, aluminum-2-ethylhexylate, and the like, mix There can be further used those readily soluble alumi tures of these substances or mixed aluminum alcoholates. num alcoholates which are obtained by the reaction of 2,844,551 3 4. metallic aluminum and slightly hydrous alcohols, advan wise mono-basic esters with the traces of alcohol which tageously in the presence of activating agents, and which are always present. contain per 1 equivalent of aluminum about 0.5 to 0.8 These compounds can belong to the aliphatic, isocyclic, alkoxy groups. - aromatic or heterocyclic series and can contain further As aluminum alcoholates containing halogen atoms indifferent substituents of neutral nature, for instance there may be mentioned, for instance: readily soluble halogen atoms, or groups, such as the groups OH or aluminum alcoholates containing halogen, corresponding SH, or ether, thioether or ester groups, carboxylic acid for instance to the formula AlHal(OR)2 or Al-Hals (OR), amide or urea groups or the like. This chain of carbon wherein R stands for low aliphatic radicals, such as atoms can be interrupted by heteroatoms such as O, N, AlCl(OC2H5)2, and obtainable by causing aliphatic alco or S. hols to react upon aluminum chloride, as described by As aliphatic mono-carboxylic acids may be mentioned, Mpetse (Chemisches Zentralblatt, 1931, II, 1691). for example: formic acid, acetic acid, propionic acid, Readily soluble aluminum alcoholates of that kind con butyric acid, caproic acid, caprylic acid, capric acid, taining halogen can also be obtained, according to the stearic acid, oleic acid, palmitic acid, lauric acid, myristic process described in German Patent No. 859,143, by re 5 acid, behemic acid, montanic acid, mixtures of acids ob acting a theoretically insufficient quantity of alcohols with tained by oxidation of paraffin, resin acids, such as abietic aluminum halides in the presence of ammonia or amines. acid or colophony. Instead of single acids there can also Furthermore, there may be mentioned: aluminum alco be used mixtures of the acids mentioned or mixtures holates containing halogen or being free from halogen of acids which are obtained from natural products, if and corresponding to the formula AlHal (ORC), 20 necessary hydrogenated. Mixtures of this kind are, for In-m-3, m being at least 1, R standing for an alkylene instance, the fatty acids of sperm oil, coconut oil, tall radical. These substances can be obtained by reacting oil, inseed oil, soybean oil, fish oil, cottonseed oil, train. aluminum halides with alkylene oxides, AICl(OCHCI), oil, peanut oil, sulfocarbon oil, rape oil, tallow animal for instance, can be obtained by reacting 2 moles of oil, bone fat, lard, tung oil. There may further be men ethylene oxide. with aluminum chloride. 25 tioned, for example, acrylic acid or methacrylic acid, In halogenated aluminum alcoholates of that kind, part crotonic acid, methoxyacetic acid, ethoxyacetic acid, of the radicals bound in an ether-like manner can, fur butoxyacetic acid, dodecyloxyacetic acid, chloroacetic thermore, be split off by thermal or hydrolytic after-treat acid, a-chloropropionic acid, (3-chloropropionic acid, oz ment; it is probable that in most cases the aluminum chlorobutyric acid, thioglycolic acid, thiolactic acid, atoms are linked together in chain-fashion through oxygen 30 malonic acid mono-ethyl ester, oxalic acid mono ethyl bridges.
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